24526-69-0

Basic information

• Product Name: 3-CYANO-4-METHYLCOUMARIN
• Synonyms: 4-METHYL-2-OXO-2H-CHROMENE-3-CARBONITRILE;3-CYANO-4-METHYLCOUMARIN;3-CYANO-4-METHYLCOUMARIN 97%;4-methyl-2-oxochromene-3-carbonitrile
• CAS NO: 24526-69-0
• Molecular Formula: C₁₁H₇NO₂
• Molecular Weight: 185.18
• Product Categories: Coumarins;Building Blocks;Heterocyclic Building Blocks
• Mol File: 24526-69-0.mol
• Article Data: 20

Chemical Properties

• Melting Point: 192-195 °C (dec.)(lit.)
• Boiling Point: 352.2°Cat760mmHg
• Flash Point: 168.1°C
• Appearance: /
• Density: 1.29g/cm³
• Vapor Pressure: 3.9E-05mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• CAS DataBase Reference: 3-CYANO-4-METHYLCOUMARIN(CAS DataBase Reference)
• NIST Chemistry Reference: 3-CYANO-4-METHYLCOUMARIN(24526-69-0)
• EPA Substance Registry System: 3-CYANO-4-METHYLCOUMARIN(24526-69-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 24526-69-0(Hazardous Substances Data)

Usage

Description

3-Cyano-4-methylcoumarin, also known as 4-Methyl-2-oxo-2H-chromene-3-carbonitrile, is a 3-substituted 4-methylcoumarin derivative. It has been studied for its structural properties, vibrational frequencies, and electronic spectra using density functional theory (DFT). 3-CYANO-4-METHYLCOUMARIN is formed during the Knoevenagel condensation of o-hydroxyacetophenone with ethyl cyanoacetate, catalyzed by calcined Mg-Al hydrotalcite.

Uses

Used in Organic Synthesis:
3-Cyano-4-methylcoumarin is used as a reactant for various organic reactions and the synthesis of organic compounds. Its unique structure and properties make it a valuable component in the creation of a wide range of chemical products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Cyano-4-methylcoumarin is used as a key intermediate in the synthesis of various drugs and drug candidates. Its versatility in organic synthesis allows for the development of new medications with potential therapeutic applications.
Used in Chemical Research:
3-Cyano-4-methylcoumarin is also utilized in chemical research as a model compound for studying various chemical reactions and mechanisms. Its properties and reactivity provide valuable insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.
Used in Material Science:
In the field of material science, 3-Cyano-4-methylcoumarin may be employed in the development of new materials with specific properties, such as optical, electronic, or mechanical characteristics. Its unique structure and functional groups can be exploited to create novel materials with potential applications in various industries.

Synthesis Reference(s)

Journal of the American Chemical Society, 75, p. 1886, 1953 DOI: 10.1021/ja01104a032

InChI:InChI=1/C11H7NO2/c1-7-8-4-2-3-5-10(8)14-11(13)9(7)6-12/h2-5H,1H3

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 107-91-5 cyanoacetic acid amide 
• 14974-24-4 2,2-difluoro-4-methyl-benzo-1,3,2-2H-dioxaborine 
• 105-56-6 ethyl 2-cyanoacetate 
• 108-24-7 acetic anhydride 
• 17831-88-8 4-chloro-2H-1-benzopyran-2-one 
• 41078-17-5 3-cyano-4-methyl-benzopyran-2-imine 
• 109-77-3 malononitrile 
• 24526-79-2 Cyano-(2-oxo-2H-chromen-4-yl)-acetic acid ethyl ester 

Downstream Products

• 134305-32-1 3-amino-4-cyano-5-(3-thienyl)benzocoumarin 
• 607-71-6 4-methyl-2H-chromen-2-one 

Relevant articles and documents

Synthesis and optical properties of new 2-oxo-4-vinyl-2H-chromene-3-carbonitrile dyes

New derivatives of 2-oxo-4-vinyl-2H-chromene-3-carbonitrile have been synthesized by the Knoevenagel reaction of 4-methyl-2-oxo-2H-chromene-3-carbonitrile with aromatic and heteroaromatic aldehydes. The first hyperpolarizability β for the obtained compoun

Easy solventless synthesis of new mono and bis amino-5H-chromeno [3,4-c] pyridin-5-one derivatives

A new series of mono and bis amino-5H-chromeno [3,4-c] pyridin-5-one derivatives were prepared via the reaction of primary amines with 4-(2-(dimethylamino)vinyl)-2-oxo-2H-chromene-3-carbonitrile 3. The X-rays structures of 4-(hexylamino)-5H-chromeno[3.4-c

On the Condensation of 2,2-Difluoro-4-methyl-benzo[d]-1,3,2-dioxaborines with Cyano Acetic Acid Derivatives. Formation and Transformation of 3-Cyano-4-methyl-benzo [b]pyran-2-ones and their 2-Imine Precursors

By condensation of 2,2-difluoro-4-methyl-benzo[d]-1,3,2-2H-dioxaborines(12) with cyano acetic acid derivatives in presence of weak bases, 3-cyano-4-methyl-benzo[b]pyran-2-ones (13) or their 3-cyano-4-methyl-benzo[b]pyran-2-imine precursors (14) are available in satisfactory yields.

One-Pot Green Synthesis of 2-Oxo-2H-chromene-3-carbonitriles Using Dual-Frequency Ultrasonication

Abstract: A green synthesis of 2-oxo-2H-chromene-3-carbonitriles has been carried out in one step by reacting 2-hydroxybenzaldehydes or 2-hydroxyacetophenones with ethyl cyanoacetate under dual-frequency ultrasonica-tion (ultrasonic bath of 40 KHz and probe of 20 KHz). The compounds were obtained in very high yield, and their structures were confirmed by IR and NMR data.

Zirconium(IV) oxychloride: A simple and efficient catalyst for the synthesis of chromen-2-one derivatives

The present work explores a highly efficient, environmental friendly, green protocol for the synthesis of chromen-2-one derivatives (3a-m) by the condensation of salicylaldehydes with various active methylene compounds using zirconium (IV) oxychloride as catalyst. This is a convenient and rapid method for Knoevenagel condensation and this methodology offers several advantages including shorter reaction time, milder conditions, inexpensive catalyst, simple operational procedure and allowed to achieve the desired products in excellent yields. The structures of all the synthesized compounds were confirmed by spectral data.